One more strange and unexpected import case.
Common import (without multiple, but with expected CSS output) doesn't happen if the same file was already reference-imported earlier.
The fileset to reproduce:
main.less
@import 'foo';
@import 'bar';
bar.less
@bar-height: 42px;
.bar {
    height: @bar-height;
}foo.less
@import (reference) 'bar';
.foo {
    padding-top: @bar-height;
}Expected CSS output for main.less compiled:
.foo {
    padding-top: 42px;
}
.bar {
    height: 42px;
}Actual CSS output for main.less compiled:
.foo {
    padding-top: 42px;
}